EP0040985B1 - Process for the recovery of pure acetone from cumene hydroperoxide cleavage reaction product - Google Patents

Process for the recovery of pure acetone from cumene hydroperoxide cleavage reaction product Download PDF

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Publication number
EP0040985B1
EP0040985B1 EP81302315A EP81302315A EP0040985B1 EP 0040985 B1 EP0040985 B1 EP 0040985B1 EP 81302315 A EP81302315 A EP 81302315A EP 81302315 A EP81302315 A EP 81302315A EP 0040985 B1 EP0040985 B1 EP 0040985B1
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EP
European Patent Office
Prior art keywords
column
acetone
fraction
process according
vapour
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP81302315A
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German (de)
English (en)
French (fr)
Other versions
EP0040985A2 (en
EP0040985A3 (en
Inventor
Robert George Bp Chemicals Limited Laverick
James Mann Bp Chemicals Limited Scotland
William Robertson Bp Chemicals Limited Mitchell
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BP Chemicals Ltd
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BP Chemicals Ltd
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Publication of EP0040985A2 publication Critical patent/EP0040985A2/en
Publication of EP0040985A3 publication Critical patent/EP0040985A3/en
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Publication of EP0040985B1 publication Critical patent/EP0040985B1/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S203/00—Distillation: processes, separatory
    • Y10S203/20—Power plant

Definitions

  • the present invention is directed to the process for the production of phenol and acetone by cleavage of cumene hydroperoxide and in particular to a process for the recovery of pure acetone from the crude acetone obtained from the fractional distillation of cumene hydroperoxide cleavage reaction product.
  • the cleavage of cumene hydroperoxide produces phenol and acetone and varying amounts of side-products such as aldehydes, methanol, mesityl oxide, hydroxyacetone, alphamethylstyrene, acetophenone, cumyl phenols, phenyldimethyl carbinol ("carbinol”), organic acids, other higher phenols and high-boilers.
  • side-products such as aldehydes, methanol, mesityl oxide, hydroxyacetone, alphamethylstyrene, acetophenone, cumyl phenols, phenyldimethyl carbinol (“carbinol”), organic acids, other higher phenols and high-boilers.
  • the cumene hydroperoxide cleavage reaction product after removal of any cleavage catalyst which may be present, is fed to a distillation column, hereinafter referred to as the crude acetone column, wherein there is removed overhead a crude acetone fraction containing material present in the feed with a boiling point lowerthan that of phenol and there is taken from the bottom of the column a fraction containing phenol, carbinol, acetophenone, cumyl phenols, higher phenols and high-boilers from which phenol is recovered in a series of fraction distillations.
  • a distillation column hereinafter referred to as the crude acetone column
  • the crude acetone fraction removed overhead is condensed and part of the condensate is returned to the column as reflux.
  • the crude acetone consisting the remainder of the condensate is not sufficiently pure to meet the requirements of British Standard Specification BS 509:1971 or to meet a typical commercial grade which is as follows: The tests relating to the specification are carried out in accordance with the methods described in British Standard Specification BS 509:1971.
  • the crude acetone does not meet the specification for permanganate time which requires that the colour of potassium permanganate added to the acetone be retained for at least 2t hours. Accordingly the crude acetone is further purified by a combination of chemical treatment and distillation.
  • the nature and extent of the impurities present in the crude acetone fraction depend to some extent on the manner in which the process is operated. Relevant factors include for example the conditions under which the cumene hydroperoxide is cleaved and the mode of operating the crude acetone column.
  • Impurities believed to be responsible for failure of the crude acetone to meet the specification for permanganate time are aldehydes such as acetaldehyde and propionaldehydes, and also mesityl oxide.
  • the crude acetone normally also contains water to a greater or lesser extent hydrocarbons such as cumene and alphamethylstyrene, traces of organic acids such as formic and acetic acids and less than about 3% w/w phenol.
  • hydrocarbons such as cumene and alphamethylstyrene
  • traces of organic acids such as formic and acetic acids and less than about 3% w/w phenol.
  • Other impurities which may be present in the crude acetone and may contribute to its failure to meet the specification are methanol and hydroxyacetone.
  • the present invention provides a process for the recovery of pure acetone from a crude acetone fraction removed overhead as a vapour from a first column separating phenol and higher-boiling compounds as a bottom fraction from the cumene hydroperoxide cleavage reaction product which process comprises partially condensing the crude acetone fraction, returning the condensed portion of the crude acetone fraction to the first column as reflux, feeding the remaining portion of the crude acetone fraction whilst still in the vapour phase to an intermediate point in a second distillation column to which there is also continuously fed at a point above the acetone feedpoint a dilute aqueous solution of an alkaline material, removing from the base of the second column a residue fraction comprising compounds boiling above acetone, removing from a point in the second column intermediate between the alkaline material feed point and the top of the column as a liquid sidedraw fraction pure acetone having a permanganate time greater than 4 hours, and removing from the top of the second column as a va
  • the alkaline material may suitably be an alkali or alkaline earth metal oxide, hydroxide or phenate, of which the alkali metal hydroxide is preferred.
  • the alkali metal hydroxide is sodium hydroxide.
  • the rate at which the alkaline material is fed to the second column is suitably such that the concentration of the alkaline material in the residue fraction removed from the base of the column is in the range 0.01 to 5.0, preferably 0.2 to 0.4% w/w.
  • the second column is preferably operated at a reduced pressure in the range 0.3 to 0.8, preferably in the range 0.5 to 0.7 bar absolute at the top of the column.
  • the residue fraction removed from the base of the second solumn will invariably contain a minor proportion of the acetone fed to the column in addition to compounds boiling above acetone.
  • a reboiler Suitably the reboiler may be maintained at a temperature in the range 80 to 120, preferably in the range 85 to 100°C, which temperatures pertain to a pressure of 0.6 bar at the column top. For other pressures at the column top the temperature ranges should be adjusted appropriately.
  • the reflux to sidedraw ratio in the second column may suitably be in the range 4:1 to 25:1, depending upon the proportion of condensate from the second column which is recycled to another part of the phenol from cumene process.
  • FIG. 1 is a simplified schematic flow diagram showing a preferred arrangement of equipment useful in the performance of the process of the invention.
  • 1 is a single distillation column containing 55 plates or trays operating under reduced pressure, only plates 1, 10, 20, 45 and 55 being illustrated for reason of simplicity.
  • the column is provided with a conventional reboiler 2 connected to a source of heat, a condenser 3 for condensing the vapours leaving the column, outlet 4 for withdrawing a residue fraction from the base of the column, crude acetone fraction vapour feed inlet 5, aqueous alkaline solution inlet 6, purified acetone outlet 7, pipe 8 for conveying vapour removed overhead to the condenser 3, pipe 9 for conveying the condensed vapour to a holding drum 10, pipe 11 for returning part of the condensate if reflux to the column and W iwi 12 for recycling the remainder of the condensate.
  • a crude acetone fraction comprising acetone, hydrocarbon, water, aldehydes, mesityl oxide, methanol, hydroxyacetone and less than 1% w/w phenol, obtained as a vapour fraction by partial condensation of the vapour fraction removed from the top of a column (not shown) in which a phenol-containing fraction is separated and removed as a base fraction from the catalyst-free cumene hydroperoxide cleavage reaction product, is continuously fed through inlet 5 which is located about 10 trays above the bottom of the column 1.
  • a dilute aqueous solution of an alkali which mixes with the downflowing liquid in the column and serves to scrub the upflowing vapours.
  • the dilute aqueous alkali removes aldehydes and any hydroxyacetone by promoting aldol condensation reactions thereby producing high-boilers.
  • the dilute aqueous alkali also removes any phenol present as sodium phenate and organic acids as their sodium salts.
  • Removed from the base of column 1 through pipe 4 is a fraction composed mainly of compounds having a higher boiling point than acetone such as excess alkaline material, water, mesityl oxide, sodium phenate, sodium acetate, sodium formate and high-boiling imurities together with a small proportion of the acetone in the feed.
  • the temperature of the reboiler 2 is maintained at such a valve that the proportion of acetone in the residue fraction removed from the base of column 1 is minimised.
  • Acetone of purity meeting the requirements of British Standard Specification BS 509:1971 and in particular having a permanganate time greater than 4 hours is removed through pipe 7 at a point about 45 trays above the base of the column as a liquid sidedraw fraction.
  • Acetone having a lower permanganate time than the liquid sidedraw fraction by reason of its higher aldehyde content and containing also methanol but having a lower water content is removed from the top of column 1 through pipe 8 as a vapour fraction.
  • the vapour fraction is condensed in the condenser 3 and passes through pipe 9 into tank 10. From tank 10 part of the condensate is returned through pipe 11 to the top of column 1 as reflux as the remaining portion of the condensate is recycled through pipe 12 to another point in the phenol from cumene process.
  • the purity of the liquid acetone sidedraw fraction can be improved beyond the requirements of BS 509:1971 to that demanded by present day commercial specifications for industrial acetone by selection of optimum process conditions.
  • the crude acetone vapour was obtained by feeding catalvst-free cumene hydroperoxide cleavage reaction product to a first distillation column wherein there is removed overhead a crude acetone vapour fraction containing material present in the feed with a boiling point lower than that of phenol and there is taken from the bottom of the column phenol and higher-boiling compounds.
  • the crude acetone fraction removed overhead is partially condensed and the condensate is returned to the column as reflux.
  • the remainder of the crude acetone fraction is used as the vapour feed in the Examples.
  • Crude acetone vapour containing impurities such as aldehydes (660 ppm), hydroxyacetone (4000 ppm), phenol (2800 ppm) and water was . continuously fed to a 50 mm diameter 55 plate Oldershaw column fitted with a conventional reboiler maintained at 88°C. The pressure at' the top of the column was 0.6 bar. The feed was introduced on tray 10 at a rate of 875 ml.h-' and a 1% w/w aqueous sodium hydroxide solution was fed to plate 20 at a rate of 300 ml.h- 1 .
  • Liquid acetone satisfying the purity requirements of British Standard Specification BS 509:1971 and in particular having a permanganate time (PMT) in excess of 4 hours was removed as a sidedraw from plate 45.
  • Impure acetone having a PMT lower than that of the sidedraw acetone was removed as an overhead distillate, condensed and part of the convensate was returned as reflux to the top of the column.
  • the reflux ratio (reflux to sidedraw) was 4.6:1. Water, excess alkali, sodium phenate, sodium acetate, sodium formate, high-boiling materials and a little acetone was removed as a residue fraction from the base.
  • Example 1 The procedure of Example 1 was repeated except that an equivalent weight of 2% sodium hydroxide was added to plate 20.
  • the liquid acetone removed as a sidedraw conformed to BS 509:1971 and in particular had a PMT in excess of 4 hours.
  • Example 4 was repeated except that the crude acetone vapour was fed to the column at 1120mlh-1, a 5% w/w aqueous sodium hydroxide solution was added to the column at a rate of 50 ml h- 1 , the reboiler was maintained at 95°C and the reflux to sidedraw ratio was 6.2:1.
  • the liquid acetone sidedraw met BS 509:1971 and in particular had a PMT greater than 4 hours.
  • the PMT of the acetone distillate removed overhead was less than of the sidedraw.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP81302315A 1980-05-27 1981-05-26 Process for the recovery of pure acetone from cumene hydroperoxide cleavage reaction product Expired EP0040985B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8017367 1980-05-27
GB8017367 1980-05-27

Publications (3)

Publication Number Publication Date
EP0040985A2 EP0040985A2 (en) 1981-12-02
EP0040985A3 EP0040985A3 (en) 1982-03-24
EP0040985B1 true EP0040985B1 (en) 1983-07-27

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EP81302315A Expired EP0040985B1 (en) 1980-05-27 1981-05-26 Process for the recovery of pure acetone from cumene hydroperoxide cleavage reaction product

Country Status (5)

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US (1) US4340447A (ko)
EP (1) EP0040985B1 (ko)
JP (1) JPS5745127A (ko)
CA (1) CA1165330A (ko)
DE (1) DE3160695D1 (ko)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1948595A1 (en) * 2005-11-14 2008-07-30 Sunoco, Inc. (R&M) Process for recovery of cumene hydroperoxide decomposition products by distillation

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JPH062703B2 (ja) * 1986-02-15 1994-01-12 三菱化成株式会社 ジアセトンアルコ−ルの精製法
US4722769A (en) * 1986-04-24 1988-02-02 Allied Corporation Process for recovery of acetone
US4824527A (en) * 1986-06-10 1989-04-25 Erickson Donald C Nested enrichment cascade distillation of unequal mixtures
US4675082A (en) * 1986-09-22 1987-06-23 Atlantic Richfield Company Recovery of propylene glycol mono t-butoxy ether
JPH0276348U (ko) * 1988-11-30 1990-06-12
IT1276823B1 (it) * 1995-10-06 1997-11-03 Enichem Spa Procedimento per la purificazione dell'acetone
US6340777B1 (en) 1999-10-22 2002-01-22 General Electric Company Method for purifying acetone
US6331654B1 (en) * 2000-02-10 2001-12-18 Illa International Llc Method of production of product acetone of high stability to oxidation
DE10060505A1 (de) * 2000-12-06 2003-01-30 Phenolchemie Gmbh & Co Kg Verfahren zur Abtrennung von Phenol aus einem Gemisch, welches zumindest Hydroxyaceton, Cumol, Wasser und Phenol aufweist
US7416645B2 (en) * 2002-07-11 2008-08-26 Ineos Phenol Gmbh & Co. Kg Continuous process for recovering acetone from a waste stream resulting from acetone purification
US7626060B2 (en) * 2003-07-11 2009-12-01 INEOS Phenol GmbH & Co., KG Process for the preparation of phenolic compounds, for separating phenol from cleavage product mixtures, and an apparatus
US7141700B1 (en) * 2005-08-19 2006-11-28 Uop Llc Decomposition of cumene hydroperoxide
US7888537B2 (en) * 2006-12-29 2011-02-15 Uop Llc Solid acid catalyst and process for decomposition of cumene hydroperoxide
RU2400469C2 (ru) * 2008-12-09 2010-09-27 Общество с ограниченной ответственностью "Новые технологии" Способ очистки ацетона-сырца
RU2403236C2 (ru) * 2008-12-09 2010-11-10 Общество с ограниченной ответственностью "Новые технологии" Способ очистки ацетона
JP5614260B2 (ja) * 2010-11-25 2014-10-29 コニカミノルタ株式会社 光学素子の保存方法、及び分析チップの保存方法
WO2013043606A1 (en) * 2011-09-19 2013-03-28 Kellogg Brown & Root Llc Dividing wall column for alpha-methylstyrene and cumene distillation
US8710274B2 (en) 2012-05-04 2014-04-29 Lyondell Chemical Technology, L.P. Method of purifying crude acetone stream
US8889915B2 (en) * 2013-03-14 2014-11-18 Kellogg Brown & Root Llc Methods and systems for separating acetone and phenol from one another
KR101979771B1 (ko) * 2015-06-30 2019-05-17 주식회사 엘지화학 증류 장치
ES2967529T3 (es) 2016-07-12 2024-04-30 Sabic Global Technologies Bv Sistemas y métodos de purificación de acetona
JP2023531469A (ja) 2020-06-19 2023-07-24 ケロッグ ブラウン アンド ルート エルエルシー アセトンの回収及び精製
US11001548B1 (en) * 2020-07-17 2021-05-11 Kellogg Brown & Root Llc Method of producing acetone with low aldehydes content
CN116023245B (zh) * 2023-01-31 2024-03-29 实友化工（扬州）有限公司 一种丙酮深度精馏过程中碱水浓度的控制方法

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1948595A1 (en) * 2005-11-14 2008-07-30 Sunoco, Inc. (R&M) Process for recovery of cumene hydroperoxide decomposition products by distillation
EP1948595A4 (en) * 2005-11-14 2010-10-13 Sunoco Inc R&M PROCESS FOR THE DISTILLATION RECOVERY OF DECOMPOSITION PRODUCTS OF CUMENE HYDROPEROXIDE

Also Published As

Publication number Publication date
JPS6412251B2 (ko) 1989-02-28
CA1165330A (en) 1984-04-10
JPS5745127A (en) 1982-03-13
DE3160695D1 (en) 1983-09-01
EP0040985A2 (en) 1981-12-02
EP0040985A3 (en) 1982-03-24
US4340447A (en) 1982-07-20

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